Vincent & Whittemore
Real Estate
Bedford, New York
Tel: (914) 234-3642
Email: info(at)vinwhit(dotted)com

Lewisboro, N.Y.

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Lewisboro includes the hamlets of South Salem, Cross River, Goldens Bridge, Waccabuc, Vista and Lewisboro. This rural area has been gifted with an abundance of water. Enchanting lake homes are numerous around Truesdale Lake, Lake Waccabuc, Lake Katonah, Lake Kitchawan and the twin lakes of Oscaleta and Rippowam. Swimming, canoeing, sailing and fishing are among the activities available to lakeside residents.

Lewisboro has many facets. The southeast section borders the town of Pound Ridge and echoes that landscape with rugged rock outcroppings and varied topography. Bedford lies along the southwestern boundary and North Salem is on the north side, so Lewisboro is close to horse country. The eastern side borders Fairfield County, CT.

Many of Westchester’s antique, revolutionary houses are tucked away throughout Lewisboro. A large part of the Pound Ridge Reservation lies in Lewisboro, providing access to 4,700 acres of hiking, camping and cross-country skiing. The renowned John Jay School system serves Lewisboro.

ACTIVE LISTINGS:

Tucked away in the peaceful and well-loved Oakridge community, this beautifully renovated 1-bedroom condo with a versatile loft/bonus room offers more than just a place to live — it offers a lifestyle. From the moment you step inside, you'll notice the attention to detail and thoughtful upgrades that set this home apart. The newly renovated kitchen with custom cabinetry is a true centerpiece, designed with both function and beauty in mind. Granite countertops glisten beneath soft lighting, while a brand-new GE range with built in convection and air fryer, and a top-of-the-line water filtration system add the perfect touches for any home chef. Natural light pours in through new Anderson windows on main level, highlighting the home’s custom designer staircase — a striking architectural feature that leads to the loft above. The loft itself offers endless possibilities and the space is yours to shape. It’s this kind of flexibility that makes this home feel far bigger and more luxurious when you see it. Custom shades on new windows provide privacy with a sleek look, while custom closet systems maximize storage for functionality. Just beyond the dining area, step through sliding glass doors onto your private back deck — a peaceful outdoor retreat surrounded by greenery. It’s the perfect spot to start your morning with coffee, unwind with a good book, or enjoy quiet evenings under the stars. Whether you're entertaining guests or enjoying solitude, this space feels like your own personal escape. The Oakridge community welcomes you with resort-style amenities: pools, tennis courts, basketball courts, and friendly neighbors who make this neighborhood feel like home. Perfectly situated with easy access to New Canaan, Ridgefield, Pound Ridge, and all of Lewisboro, you’re close to charming towns, scenic parks, and top-rated restaurants and of course the award-winning Katonah-Lewisboro School District. This isn’t just a condo — it’s a chance to live simply, stylishly, and smartly in a place that invites you to slow down and savor each day. Come take a look — your next chapter could begin right here. $439,000 Pending

144 Stone Meadow South Salem, New York

1 Beds 1 Baths 1,112 SqFt 0.012 Acres

This lovely 2-bedroom, 2-bath home in the Oakridge Development offers both comfort and versatility. The entryway leads up to a bright and inviting living room with a fireplace that flows seamlessly into the dining area and kitchen, creating a warm and open concept living space. The kitchen features a sliding glass door that opens to a deck perfect for relaxing or entertaining, where you can enjoy seasonal lake views.

The primary bedroom includes its own full bath and two spacious closets, while the second bedroom also offers generous closet space. A half hall bath completes the main level.

Upstairs, the loft space overlooks the main level and includes a separate bonus room ideal for a home office, guest room, and/or hobby space. Whether you're working from home or hosting overnight guests, this flexible layout fits a variety of needs.

Community amenities include a pool, kiddie pool, tennis courts, basketball courts, and a children’s play area. Commute with ease from New Canaan or Katonah via Metro-North. Plus, you're within walking distance to a convenient shopping plaza. $425,000 Pending

71 Fox Run South Salem, New York

2 Beds 2 Baths 1,407 SqFt 0.012 Acres

Discover effortless luxury in this beautifully updated South Salem condominium—a perfect fusion of modern convenience and residential warmth.
Step into the welcoming living room where a charming fireplace sets the stage for intimate evenings or gracious entertaining. The thoughtfully designed layout features a generously proportioned bedroom and a versatile loft space that adapts to your lifestyle needs.
The heart of the home showcases an updated kitchen with premium appliances, flowing seamlessly into a spacious dining area. Large windows frame serene backyard views, while sliding doors open to your private deck—an ideal extension for outdoor dining and relaxation.
Exceptional Features:
Family room with cozy fireplace for year-round comfort
Formal dining room perfect for special occasions
A striking spiral staircase leads to the upper-level bonus space ideal as an office, den, or guest room
Hardwood floors and soaring ceilings throughout
Abundant natural light creates an airy, open atmosphere
Modern Updates: Central air conditioning, updated bathroom fixtures, and new washer and dryer ensure move-in readiness.
Resort-Style Amenities: The community offers dual swimming pools, tennis and basketball courts, tranquil pond views, and a children's play area.
Prime Location: Minutes from the train station with convenient access to shopping, dining, and acclaimed schools.
This exceptional residence represents the perfect balance of tranquil privacy and connected convenience. Schedule your private showing today. $425,000 Active

156 Stone Meadow South Salem, New York

1 Beds 1 Baths 1,112 SqFt 0.012 Acres

Welcome to 132 Stone Meadow, a thoughtfully designed condo nestled in the heart of South Salem’s coveted Oakridge community. With over 1,100 square feet of living space, this one-bedroom, one-bathroom home offers more than just comfort—it delivers flexibility and style. A spacious loft adds a layer of versatility, perfect for a home office, guest room, or creative studio. The open layout is bright and inviting, with soaring ceilings and natural light that pours in from every angle. Sliding glass doors lead to a private deck, where mornings begin with coffee and evenings wind down with fresh air and quiet views.
Inside, every detail has been considered. Brand-new luxury vinyl plank flooring brings warmth and modern elegance to the space, while a newly installed heater and AC unit (2024) ensure year-round comfort. Whether you're curling up with a book or entertaining friends, this home adapts beautifully to your lifestyle.
Step outside and discover the Oakridge community—a neighborhood that blends resort-style amenities with a genuine sense of belonging. Enjoy access to sparkling swimming pools, tennis and basketball courts, and scenic walking paths that invite you to explore and connect. Friendly neighbors and well-kept grounds make this a place that truly feels like home.
Location is everything, and here you’re perfectly positioned near the charming towns of New Canaan, Ridgefield, Pound Ridge, and all of Lewisboro. From top-rated restaurants and boutique shops to tranquil parks and cultural gems, everything you need is just minutes away. And with the award-winning Katonah-Lewisboro School District, this home offers long-term value in more ways than one.
This isn’t just a condo—it’s a chance to live with intention. Whether you’re downsizing, starting fresh, or searching for a weekend retreat, 132 Stone Meadow invites you to slow down, settle in, and savor each day.
Come take a look. Your next chapter starts here. $399,900 Active

132 Stone Meadow South Salem, New York

1 Beds 1 Baths 1,112 SqFt 0.014 Acres